


Secret Wingman

by Awesome_Sauce432



Series: Beaujester Week 2019 [6]
Category: Critical Role (Web Series)
Genre: Beaujester Week 2019, Caleb Accidentally Becomes The Secret Keeper For Crushes And He Does Not Want To Be That, F/F, Mutual Pining, secret keeping
Language: English
Status: Completed
Published: 2019-07-29
Updated: 2019-07-29
Packaged: 2020-07-25 21:01:11
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,837
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20032270
Author URL: https://archiveofourown.org/users/Awesome_Sauce432/pseuds/Awesome_Sauce432
Summary: On a day while most of the Nein are out of the house, Caleb becomes privy to two separate but very related secrets. Beau is in love with Jester, Jester is in love with Beau. Both are painfully unaware of the feelings of the other. With the implicit or explicit wish from both to NOT say anything, Caleb decides to take matters into his own hands to... push things along a little.For Day 6 Of Beaujester Week, Mutual Pining!





	Secret Wingman

Caleb startled out of the book he’d been reading at the sound of an insistent knocking at his door. With all the Nein bar him, Beau and Jester out on a shopping mission, he’d been hoping for some peace and quiet, since the two girls were usually able to entertain each other. Apparently not. The knocking paused for a moment, and Caleb let himself hope that perhaps whoever it was had decided that it wasn’t important and moved on.

“Caaaaaaleb, are you in there?” Beau’s voice. Which meant moving on was highly unlikely.

Mourning the temporary loss of his concentration, Caleb closed the book and went to open the door. Sure enough, Beau was standing there, her closed hand still hovering over where the door had been, her foot tapping the ground repeatedly and generally looking slightly manic.

“Are you alright?”

Without responding, Beau darted inside, practically slamming the door shut behind her, before pacing in a circle in the middle of his room. Caleb stood there for a moment with a frown, before deciding to try speaking again. “Beau?”

She didn’t appear injured, or even particularly upset. Just… overflowing with energy, and perhaps a bit nervous. Her head flicked up in his direction, though she continued pacing. “Yeah?”

“Why are you in my room?”

“Okay. Okay, I need your opinion on something.” Beau pointed at him, before scrunching her face up and turning away, leaving Caleb realising that figuring out exactly what she wanted was probably going to be a bit of a journey.

“What do you need my opinion on?” He tried, but Beau either didn’t hear him or ignored him, continuing to wear a groove into his floor.

His frown deepening, Caleb took a step closer to Beau, bring his hands out of his pockets. “Beau, what’s going on?”

“I fucked up, dude.” Beau stopped pacing, instead switching to running a hand through her hair, the other hand planted firmly on her hips. “I _fucked up_.”

“I don’t understand what you’re talking about.”

“It’s Jester.” Beau beelined towards Caleb’s bed and sat down, tapping her toes on the floor. When she spoke, it was a little quicker than she usually talked, sounding frustrated. “We were talking and we started talking about Kiri because Jester misses her so then we started talking about Hupperdook so then we started talking about Caduceus and the Blooming Grove and _then _we started talking about Keg because Jester only really met her for like a day before Keg left and so then Jester started asking me about anyone _else _I’ve had sex with and I started talking about my old _girlfriend_-”

Caleb stood silently as Beau spoke, her arms folded tight over her chest, shoulders tense even as her toes refused to remain still. Silently, Caleb snapped his fingers and summoned Frumpkin into existence on the bed, instructing him to pad up to Beau, nuzzling his head into her side.

“So she asked how me and her got together, and then she asked if I have a crush on anyone right now and I said no.” Beau shut her mouth tight, her frown darkening. “I said it… probably kinda harshly. I didn’t _mean _to, but I did.”

“Oh. Did it upset Jester?” Caleb stepped closer to Beau, not sitting down next to her but just inside the range he considered to be appropriate for emotional support. Frumpkin seemed to help a little, but not quite as much as he hoped. If Frumpkin didn’t help, there was only so much more he had to offer.

“I think so. She got like, this _look_ on her face, and then I left. To come here.” Beau’s face crumpled, and she groaned, holding her head in her hands. “Gods I fucked up.”

“Well, I do not think you fucked up _too _badly. If you apologise for sounding harsh, I’m sure Jester will understand.”

“That’s not it. I mean, that’s part of it, but that’s not _it_.” Beau’s voice was slightly stifled from her mouth being squished together by her hands, while Caleb ran through what Beau had said to try and locate some other kind of wrongdoing. Unfortunately, he was not exactly the party expert on social niceties. Frumpkin was now laying down next to Beau, seemingly mostly indifferent.

“Then what is it? Did you do something else?”

“I lied.” Beau groaned, letting herself fall backwards dramatically onto the bed, flinging her arms outwards and staring up at the ceiling. “I _do _have a crush on someone.”

“Yasha? I thought we were all aware of that.” Caleb shut his mouth when Beau just groaned again. “Am I…wrong?”

“I don’t think I’d call what I had for Yasha a crush.” Beau murmured. “An… attraction, maybe? Either way, that’s not it!”

Caleb quickly ran through the list of remaining possibilities. If it was a crush, that presumably meant it was someone Beau spent a lot of time with. Men weren’t an option, so that got rid of most of them.

“Oh.” Realisation dawned on him, and Beau just continued staring at the ceiling. “You firmly denied having a crush… to the person you have a crush on. And you may have hurt her feelings when you did it.”

Beau’s face crumpled. “I’m a fucking dumbass.”

“I don’t think you are a dumbass,” Caleb said, mentally processing the fact that Beau had a crush on Jester. Okay, retroactively he could see it, but it was still unexpected.

“If you fireball me and I don’t dodge out of the way, do you think it will kill me instantly?”

“I am not going to fireball you.” Caleb sat down on the end of his bed, and Beau accepted his declaration with only a slight huff. “I still don’t think this is as bad as you fear. Does Jester like you as well?”

“As a best friend.” Beau covered her face with her hands again. “Which is great! I love that! We’re friends, and we’re roommates and we can talk to each other and all I had to do was not let my stupid feelings get in the way, and they did and now it’s awkward.”

She spat out the word ‘awkward’ as if that was the absolute worst outcome of this entire debacle, and Caleb felt like there was little he could really do but sit and try to convince her that it was mostly alright. He wasn’t quite sure how to do that, but he’d try.

“I am sure you will be able to get through it. You and I have said awkward and harsh things to each other and we are able to still consider each other friends.”

“I don’t have a crush on you though. I didn’t run away from you after loudly declaring I _didn’t _have a crush on anyone, including you.”

“Did you use those exact words?”

“Pretty much.”

“Oh dear.”

Beau rolled over onto her stomach, her groans muffled through the blankets on the bed. It was very strange, to see _Beau _moping on his bed, and not for the first time since she’d knocked on his door, Caleb wished any of the others were here. Caduceus or Fjord would probably have a better idea of how to handle this, or Yasha or Nott. It had been far too long since Caleb had really been anywhere close to a romantic relationship.

At a bit of a loss, Caleb awkwardly patted Beau’s back, only for them both to freeze at the sound of a knock at the door.

There was a pause, and then another knock. There was only one person it could be.

Caleb was used to Beau moving quickly, but he wouldn’t be faulted for thinking he’d accidentally cast a haste spell on her for how quickly she bolted to the closest exit. Which happened to be the window. Which (though thankfully being open) was a good few feet off the ground.

Did Beau pause to climb out of the window like a normal person? Absolutely not.

Before Caleb’s mind could really catch up to the realisation that Jester, who he had just recently found out was the subject of some kind of romantic conundrum, was standing at his door waiting for him to let her in, Beau had flown out of the window like her life depended on it. He wouldn’t be surprised if she was halfway back to the Empire by the time he stood up.

“Caleb? Are you in there?” Jester sounded… nervous. Still blinking at Beau’s sudden disappearance, Caleb shook himself out of the shock, standing up and wishing for the others to return home soon.

He opened the door, seeing Jester standing there with a crestfallen look on her face. Oh dear.

“Jester? Are you alright?”

Much like Beau before her, Jester walked past him into the room, wringing her hands together and turning to face him. “Oh Caleb, I think I messed up.”

Wait, _she _messed up? Was there something else Beau hadn’t told him about whatever conversation those had had?

“What happened?” He could only hope that he looked suitably oblivious, closing the door behind her.

Thankfully, Jester didn’t seem particularly inclined to scrutinising him, biting her lip and glancing away. “I think I upset Beau.”

“Oh?”

“Yeah. We were like, talking about stuff and I asked her if she liked anyone, like if she _like liked _anyone, and she said she didn’t and she seemed kind of upset and then she ran away and I tried asking the Traveler about it but he thinks I didn’t do anything wrong but I still feel really bad.” Jester spoke very quickly, so quickly that if Caleb didn’t already know the brief synopsis of the conversation he might not have been able to follow it.

Distantly, Caleb realised that he couldn’t let Jester know that Beau had already talked about this with him. For one, her swift escape had made it clear she didn’t want Jester to know. Two, that meant that if Caleb spilled the beans, Beau might strangle him. Okay, she probably wouldn’t actually do that, but she definitely wouldn’t feel any better about the whole situation.

“Why do you feel bad?”

“Because I don’t want to upset Beau!” Jester threw her hands up in the air. “She’s so cool, and I think I asked too many questions and she got upset and she doesn’t have a crush on anyone and that _sucks_.”

Caleb mentally instructed Frumpkin to jump off the bed (where he had been recovering from the shock of Beau leaping off it without warning) and weave his way around Jester’s legs. Unlike Beau, Jester instantly took notice of the cat, dropping down to a sitting position and placing him in her lap, patting him repetitively.

“It’s so _stupid_, she’s been okay with me asking questions like that before but I must’ve gone too far and now I ruined it!” Her head fell forward to rest on Frumpkin, and Caleb quietly sat down opposite her.

“I’m sure it will be okay.” Caleb grimaced a little, trying to think of something to say that wouldn’t reveal anything Beau had told him. “Beau’s your best friend, isn’t she?”

Jester looked up, a pout on her face. “_Yeah, _but that just makes it worse! Good best friends don’t upset each other!”

“I consider Beau to be one of my best friends, and she and I have said things that upset each other multiple times. I am sure Beau will forgive you.”

Jester didn’t respond to that for a few moments, hugging and petting Frumpkin and avoiding making eye contact with Caleb. Which, since Caleb often didn’t make eye contact with people, he noticed immediately.

She didn’t seem extremely comforted, so Caleb had to wonder if there was something he was missing once again. What had she said she was upset by? Upsetting Beau, the fact that Beau didn’t have a crush on anyone…

“Wait, you said Beau said she didn’t have a crush on anyone?” He frowned, trying to keep everything straight in his head. He just wasn’t made for this.

“No,” Jester said forlornly. Almost a little too forlornly.

“And… this is upsetting for you?” Caleb spoke slowly and evenly, keeping a careful eye on Jester’s reaction.

She paused for a while, the silence hanging in the air like a heavy blanket. Finally, she nodded.

“Why? Did you think she had a crush on someone?”

When she spoke again, Jester’s voice was quiet, wincing with almost every word. “I… _hoped _she did.”

“You hoped?” Caleb paused, another realisation slowly building his head. “Who did you hope she had a crush on?”

Another long pause. Jester was looking down at Frumpkin again, until she looked up at the ceiling, closing her eyes tight and scrunching her nose together as she spoke. “Me…”

Caleb just sat there for a moment. Ah. Okay.

Jester had a crush on Beau.

Beau had a crush on Jester.

Both thought they had just messed up their friendship.

Both of them had confessed all of this to him, with the implicit wish for him _not _to tell the other.

Oh, gods, this was going to kill him.

Jester glanced at him, presumably mistaking his blank-faced look of slowly growing horror for some kind of rejection, standing up and beginning to pace in a line.

“Oh, I shouldn’t have said that. You _can’t _tell Beau, okay Caleb? You can’t!” Jester was still hugging Frumpkin tight to her chest, looking more upset by the moment.

Caleb quickly scrambled to his feet, knowing that he was not going to be able to come up with a solution to this very quickly. Right now, the best he could do was damage control. “I won’t, I promise.”

“Okay.” Jester seemed slightly mollified with that, only for her face to fall again. “But she’s still upset!”

“As I said, I think she will easily forgive you.” Caleb decided to take a chance and rested a hand on Jester’s shoulder like Beau would do for him when he looked through Frumpkin’s eyes. Jester stopped stock-still in her tracks, her face tilting towards him.

“Yeah? You think so?”

“Ja. She is your best friend, I think she cares very deeply for you.” His could swear his eye twitched as he said it, but he could feel Jester’s shoulders relax under his hand.

“Right. If I go apologise, and I won’t ask her about crushes anymore, and then everything will be fine!” She brightened up a little, and Caleb’s encouraging smile couldn’t have felt more forced.

Without much ceremony, Jester pushed Frumpkin into Caleb’s arms, striding towards the door. “Okay! Okay, this is fine! Beau will never find out, I’ll make everything fine again, and it will all go back to normal!” She announced as she went, seemingly more for her benefit than Caleb’s.

She threw open the door, inhaling deeply before leaving, starting to call out Beau’s name.

Silently, Caleb walked to the window, watching Beau (who had retreated to a far end of what qualified as their backyard) panic for a few moments before promptly dropping into pushups, pretending to be totally chill when Jester finally spotted her, running up to her.

He couldn’t tell what they were saying, but he watched their body language shift from awkward to relieved, both seeming to quickly (and not at all eloquently) give each other apologies, before finally hugging.

That was one problem solved, he supposed. But it still left him with another.

Namely, both Beau and Jester were in love with the other, but somehow completely oblivious to the others feelings.

And he was stuck as the only one who knew it.

* * *

It took about three days before Caleb decided he really needed to do something about this. On the surface, things did indeed seem to go back to normal. As far as Caleb knew, Beau and Jester didn’t even tell any of the others about the minor crisis that had occurred while they’d been away.

But Caleb knew. And Beau and Jester both individually knew that he knew. Which now meant that whenever one of them did something particularly impressive or nice or sweet or exciting, the other would give him a ‘look’. A look that just said ‘you see what I have to deal with? You see how amazing she is?’, and then later that day they would manage to find a moment alone with him to rave about how incredible the other was. While Caleb was happy to listen to his friends gush about his other friends, knowing the context behind it made it all slightly infuriating in the way that it was infuriating to try and teach a child a magic spell that they were _so close _to understanding, but still not quite getting it.

He had to stop this before it drove him insane.

And somehow, he had to do it without tipping off the two women since they both seemed content to pine for eternity rather than risk any kind of confession possibly going wrong. Caleb could understand the anxiety, but as long as he played his cards right, hopefully everything would work out fine.

It was time for him to summon every romantic bone in his body. It was time to be the best secret wingman ever.

His plan was simple. Simple, but unmistakable. He was not going to leave any room for doubt if he could help it.

It took him a night of planning, and then half a day of set up. Thankfully most of the others were preoccupied with their own projects or errands that no one bothered him. Nott even seemed pleased he was getting some exercise rather than holing up in his room for the day. Eventually, he was prepared. Nothing left to do but execute his plan and hope he survived to the next morning.

He found Jester playing with Nugget in what had been dubbed the Happy Room, explaining that he had a magic problem he wanted to try and work through with her, citing the possibility that her clerical prowess might offer some new insight. Jester was happy to help and happier to show off her own magic, almost skipping ahead of him to his room where he told her to wait for a few minutes while he collected a few more things he needed.

Instead, he went and found Beau where she had been practising her sparring against a tree, saying he was fiddling around with his haste spell and wanted to test out some potential new capabilities, with her as a test subject. Once she was assured it wouldn’t kill her, she agreed.

“So what kind of new stuff do you think you’ll be able to do with it?” Beau asked as they walked down to Caleb’s room.

“Just making it more efficient. Last longer, increase its potency, things like that.” Caleb said vaguely, eyeing the ajar door to his room. When they got to it he stepped aside to let Beau step in first.

“Jester?”

“Beau?” Confusion was plain in both girls voices, but even as they both began to ask Caleb what was going on, he simply grabbed the door handle and shoved it closed. Immediately he cast Arcane Lock on the door, hearing a light click and another betrayed shout from within the room, followed by futile tugging on the door.

“Caleb!? What’s the big idea?” There was a distinct sound of a foot hitting the door, and Caleb winced.

“Hopefully, you will thank me for this.” He said quietly, slapping another arcane lock on the door just for good measure — even though he knew perfectly well it didn’t change anything — before slipping into Frumpkin’s eyes, who he had instructed to stay in the room while he went and fetched the girls.

Through his familiar’s vision, he could indeed see Beau kicking the door, and if she did that any longer she’d probably actually have a fairly good shot at breaking it down. Jester was sitting on Caleb’s bed where he’d left her waiting before, mostly just looking confused and slightly irritated. Neither of them were paying attention to Frumpkin. Good.

Silently, the cat crawled out from where he’d been lounging on Caleb’s desk, jumping gracefully down to the floor before leaping back up onto the bed, heading to where it met the back wall of the room. Hanging on the wall, precariously folded up so that the single tug of a rope would let it be properly revealed, was a banner that Caleb had used an unfortunate amount of ink on.

Frumpkin leaped into the air to grab onto the rope, and the banner fell open, revealing its inky message. Beau and Jester both spun around at the sound of the canvas unfolding, eyes widening as they read what was on it.

“You’re both in… love… with… each other…” Jester read aloud, while Beau inhaled sharply. Jester tilted her head, squinting at the slightly smaller message below the main one. “Please just confess.”

There was silence. Neither woman was looking at the other, both staring at the banner. Neither of them even seemed to really register Frumpkin’s presence yet, so Caleb continued looking through his familiar’s eyes, waiting for whatever would happen next.

Beau exhaled slowly, holding her hands together up to her chin. When she first spoke, she sounded almost breathless. “What the _fuuuuuck_-”

“Confess?” Jester’s voice, on the other hand, was almost squeaky, and she suddenly whirled around to face Beau, shouting out. “Are you secretly in _love _with me?!”

Beau stammered and stuttered, her gaze flitting back to the banner before jabbing a finger in Jester’s direction. “Are _you _secretly in love with _me?_!”

“Yes!” Jester shouted out, slapping a hand over her mouth and gasping as soon as she’d said it.

“Me too!” Beau looked two steps from tearing her hair out, and for a moment both women just pointed at each other, slack-jawed and gasping.

“Why didn’t you tell me?” Jester jumped up from the bed, now standing a few feet away from Beau, her hands shaking up and down like she didn’t know what to do with them. “I thought you didn’t have a crush on anyone!”

“I didn’t want to ruin being friends! I panicked!”

“Ohmigosh I can’t believe this.” Jester was bouncing on her toes, her gaze flitting around the room. “What now? What do we do now?”

Beau’s face froze, both women looking entirely unsure of themselves in a way Caleb hadn’t really seen before. A small part of him was fascinated but mostly he was just… well, he wasn’t sure if he’d really processed it yet.

Beau and Jester continued to just stare at each other, and suddenly Caleb couldn’t help but feel a slight amusement at how both of them, usually so forceful and sure of themselves and open, were absolutely stunned. He’d gotten this far, he might as well give them a bit more of a nudge.

Snapping his vision back into his own body, he cleared his throat, hoping it caught their attention. “I believe people usually kiss once they realise they are interested in one another.” He said blandly.

“oh.” He heard throughout the door, too muffled and quiet for him to tell which one of the pair it was who said it.

“i mean, we _could_-”

“do you want to?”

“uh.... yeah.”

“hahaha cool me too~”

“I think I will go now.” Caleb sighed, snapping his fingers to summon Frumpkin to his arms. There was no response, but he supposed that technically counted as a success? Overall? Perhaps?

As he walked away he started feeling a little bit smug about it. That feeling lasted for about a minute before he realised he was now stuck outside his room until Beau and Jester came out. His shoulders deflated, and he looked back over his shoulder.

He supposed he’d just have to go find one of the others. Perhaps Yeza was doing some alchemy.

* * *

Caleb didn’t go anywhere near his room for the rest of the day just to be safe, even though he was pretty sure there was no way Beau and Jester would’ve stayed there for the whole time, though he hadn’t seen them since leaving them locked in his room.

Distantly, he realised that he _had _locked them in his room, meaning that to get out they’d either have to bust the door down or climb through the window. Hopefully, they picked the latter option.

At dinner, he only half-listened to some bickering between Nott and Fjord over seasonings, when he realised Beau and Jester were walking into the dining room. Together. Holding hands.

None of the others had noticed yet, but Caleb did. They both had giddy grins on their face, Beau winking at Jester, eliciting a giggle before they separated, collecting bowls of stew from Caduceus before sitting down next to each other. They scooted their chairs closer to one another, Jester leaning over to whisper something in Beau’s ear.

The monk nodded, and Caleb narrowed his eyes, glancing at the others to confirm they still had noticed nothing strange about this. Yeza and Yasha were both eating contentedly, Caduceus was busy pouring his own bowl, Fjord and Nott had moved on from bickering about seasonings to bickering about food in the Empire versus Port Damali, and none of them had given Beau and Jester so much as a second glance.

At least until Jester gave Beau a quick kiss on the cheek. Both Yeza and Yasha glanced up, seeming to catch it out of the corner of their eyes and blinking, as if not quite certain not to make of it. If Caduceus noticed (which he probably did), he didn’t react beyond an ever so slight widening of his ever-present lazy smile. Fjord and Nott still seemed oblivious but had at least ceased their argument in favour of actually eating their food.

Jester kissed Beau again, this time definitely with the at least passing attention of everyone. There were confused looks on faces, gears turning in brains and eyes slowly widening. Then Beau decided to return the favour, smirking at Caleb before kissing a giggling Jester so very close to her lips and that’s when the penny really dropped.

“Holy _shit_.” Nott blurted out, openly gaping.“Wait-No, _hold on, wait-”_

“You two-” Fjord held up his spoon, pointing it between Jester and Beau and squinting. “You’re… you’re an item?”

“Mayyyyybe~” Jester grinned, resting her elbows on the table.

“Oh that’s nice.” Caduceus sounded not at all surprised, and Caleb probably wouldn’t have been shocked if he’d known about their mutual crushes long before now. Not that they’d probably ever find out.

“Congratulations,” Yasha said softly, a thoughtful look on her expression. “Huh. You know, a lot of things make sense now.”

“Wait… you mean you weren’t dating up until now?” Yeza seemed completely confused, and now everyone looked at him.

“Nope. Only as of like… five hours ago.” Beau said, her smile not wavering. She had one arm looped around Jester’s waist, which did not move throughout dinner. Both of them continued to smile the whole time, stealing more than a few quick hugs and kisses on foreheads, cheeks, and shoulders.

“You thought they were dating?” Nott turned to her husband, who just held up his hands in defeat.

“They were the only ones beside us sharing a room! I didn’t want to _assume _but I figured-” He started, he and Nott quickly getting into a small debate over all the possible reasonings he’d have to assume Beau and Jester were already together.

Afterwards, Caleb began to trudge towards his room, hoping he wouldn’t arrive at a door in splinters on the ground. Before he got very far, he heard jogging footsteps behind him, and Beau and Jester quickly caught up, stopping by either side of him.

“Oh? Do you two need anything?” He asked, a little surprised they were here and not heading up to a closet or somewhere to make out or something. The first few days of a relationship could be… very affectionate.

“We wanted to thank you!” Jester threw out her arms and hugged him loosely, quickly letting him go so Beau could punch him on the shoulder.

“Yeah, dude. It was totally weird how you did it, but it worked.”

“Ja. I had a feeling you would just get awkward if I told you both in person.” He shrugged, and Beau and Jester both winced.

“Probably,” Beau chuckled. “I can’t believe we couldn’t figure it out ourselves.”

“Emotions are tricky.” Caleb murmured, and both Beau and Jester nodded in agreement, clapping him on the back and hugging him again before turning and heading towards the stairs, linking arms together and laughing as they turned the corner.

Once they were gone, Caleb found himself exhaling, a very odd weight lifted off his shoulder. Then, he found himself chuckling as he walked into his room (door thankfully intact). Perhaps he should be a wingman more often.

**Author's Note:**

> why yes i did do a beaujester week fic with Caleb as the POV yeet


End file.
